Myanmar is at a crossroads. The country’s first elections in 20 years were held in 2011. It is transitioning from an authoritarian military regime to a democratic form of governance; from a centrally-directed economy to market-oriented reforms; and from six decades of conflict to peace in the border areas. Underpinning this transition is the “people-centered” development planning approach, first introduced in the Philippines in the early 1980s. This presentation highlights key facets of contemporary urban and regional planning in Myanmar, on the basis of on-the-ground observations collected over a 12-month period in 2013-2014. These facets include: (1) military-inspired planning leadership and processes; (2) role, transfer, and dualistic spatial structure of the capital city; (3) “jade- and gems-based” local resource mobilization; (4) showcase infrastructure-driven growth; (5) center-periphery/“tradition-avant-garde” dynamics; (6) community-driven development as strategy to empower and mainstream rural communities; (7) planning in conflict-affected areas; and last but not least, (8) job opportunities for Filipino professionals framed in the context of the ASEAN culture. Various lessons and practical applications of first-hand impressions on Philippine urban and regional planning will be posited.